The draw will be made live on BT Sport following their coverage of East Fife v Rangers at the Locality Hub Bayview Stadium on Sunday.
Motherwell v Heart of Midlothian - Friday (BT Sport, 7.45pm)
Motherwell were Group E winners, scoring 13 goals and conceding none, and are aiming to continue that good cup form in the Friday night game at Fir Park against Group A winners Hearts.
Celtic v Dunfermline Athletic - Saturday
Holders Celtic begin their defence of the trophy they won against Aberdeen in December. Stevie Crawford's Dunfermline side beat St Mirren on their way to topping Group H.
Forfar Athletic v Livingston - Saturday
League 1 Forfar shocked St Johnstone on their way to qualifying as one of the best runners-up. Livingston comfortably won Group G, finishing four points clear of Ayr United and Falkirk.
Hibernian v Greenock Morton - Saturday
Hibernian were Group C winners, taking 11 points from 12. Morton were runners-up to Motherwell and became the first team to qualify for the last 16 with eight points.
Kilmarnock v Hamilton Academical - Saturday
Killie are seeking revenge for a recent Premiership defeat at Hamilton. Kilmarnock were not involved in the group stages while Accies progressed as runners-up to Partick Thistle.
Partick Thistle v Ross County - Saturday
The Jags were unbeaten in Group F while the Staggies had a 100% record in Group B. County have made an impressive start in the Premiership, beating Hamilton and drawing with Hearts.
Dundee v Aberdeen - Sunday
Dundee are yet to concede a goal in this season's Betfred Cup after winning Group D. The Dons have a great recent record against the Dark Blues but have lost to St Mirren and Rijeka in the past week.
East Fife v Rangers - Sunday (BT Sport, 3.00pm)
League 1 East Fife beat Dundee United and drew with Hearts to reach this stage but they are massive underdogs against Steven Gerrard's side, who have made a great start to the season at home and in Europe.